Highly efficient electrophilic cyclization of N′-(2-alkynylbenzylidene)hydrazides

Tetrahedron Letters

Volumn 50, Issue 3, 2009, Pages 340-342

  Ding, Qiuping ^b   Chen, Zhiyuan ^a   Yu, Xingxin ^a   Peng, Yiyuan ^b   Wu, Jie ^a,c  

^a FUDAN UNIVERSITY   (China)

^b JIANGXI NORMAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Bromine; Electrophilic cyclization; Iodine; Isoquinolinium 2 yl amide; N (2 Alkynylbenzylidene)hydrazide

Indexed keywords

BENZYLIDENE DERIVATIVE; BROMINE; DICHLOROMETHANE; HYDRAZIDE DERIVATIVE; IODINE; ISOQUINOLINE DERIVATIVE; ISOQUINOLINIUM 2 YL AMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS;

EID: 57149138412     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.006     Document Type: Article

References (48)

1. For selected examples, see:. Walsh D.P., and Chang Y.-T. Chem. Rev. 106 (2006) 2476
2. Arya P., Chou D.T.H., and Baek M.-G. Angew. Chem., Int. Ed. 40 (2001) 339
3. Schreiber S.L. Science 287 (2000) 1964
4. Mitchison T.J. Chem. Biol. 1 (1994) 3
5. Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.L., and Michison T.J. Science 286 (1999) 971
6. Haggarty S.J., Mayer T.U., Miyamoto D.T., Fathi R., King R.W., Mitchison T.J., and Schreiber S.L. Chem. Biol. 7 (2000) 275
7. Nicolaou K.C., Pfefferkorn J.A., Schulaer F., Roecker A.J., Cao G.-Q., and Casida J.E. Chem. Biol. 7 (2000) 979
8. Gao K., and Wu J. Org. Lett. 10 (2008) 2251
9. Ding Q., and Wu J. J. Comb. Chem. 10 (2008) 541
10. Wang Z., Fan R., and Wu J. Adv. Synth. Catal. 349 (2007) 1943
11. Zhang L., and Wu J. Adv. Synth. Catal. 349 (2007) 1047
12. Ding Q., and Wu J. Org. Lett. 9 (2007) 4959
13. Gao K., and Wu J. J. Org. Chem. 72 (2007) 8611
14. Ding Q., Ye Y., Fan R., and Wu J. J. Org. Chem. 72 (2007) 5439
15. Sun W., Ding Q., Sun X., Fan R., and Wu J. J. Comb. Chem. 9 (2007) 690
16. For selected examples, see:. Bentley K.W. The Isoquinoline Alkaloids Vol. 1 (1998), Harwood Academic, Australia
17. Trotter B.W., Nanda K.K., Kett N.R., Regan C.P., Lynch J.J., Stump G.L., Kiss L., Wang J., Spencer R.H., Kane S.A., White R.B., Zhang R., Anderson K.D., Liverton N.J., McIntyre C.J., Beshore D.C., Hartman G.D., and Dinsmore C.J. J. Med. Chem. 49 (2006) 6954
18. Ramesh P., Reddy N.S., and Venkateswarlu Y. J. Nat. Prod. 62 (1999) 780
19. Oi S., Ikedou K., Takeuchi K., Ogino M., Banno Y., Tawada H., and Yamane T. PCT Int. Appl. (2002) 600 pp WO 2002062764 A1
20. Kaneda T., Takeuchi Y., Matsui H., Shimizu K., Urakawa N., and Nakajyo S. J. Pharmacol. Sci. 98 (2005) 275
21. Mikami Y., Yokoyama K., Tabeta H., Nakagaki K., and Arai T. J. Pharm. Dyn. 4 (1981) 282
22. Marchand C., Antony S., Kohn K.W., Cushman M., Ioanoviciu A., Staker B.L., Burgin A.B., Stewart L., and Pommier Y. Mol. Cancer Ther. 5 (2006) 287
23. Pettit G.R., Gaddamidi V., Herald D.L., Singh S.B., Cragg G.M., Schmidt J.M., Boettner F.E., Williams M., and Sagawa Y. J. Nat. Prod. 49 (1986) 995
24. For selected examples, see:. Bi H.-P., Guo L.-N., Duan X.-H., Gou F.-R., Huang S.-H., Liu X.-Y., and Liang Y.-M. Org. Lett. 9 (2007) 397
25. Sniady A., Wheeler K.A., and Dembinski R. Org. Lett. 7 (2005) 1769
26. Liu Y.-H., Song F.-J., and Cong L.Q. J. Org. Chem. 70 (2005) 6999
27. Peng A.Y., and Ding Y.X. Org. Lett. 6 (2004) 1119
28. Yue D., Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 10292
29. Flynn B.L., Verdier-Pinard P., and Hamel E. Org. Lett. 3 (2001) 651
30. Yue D., and Larock R.C. J. Org. Chem. 67 (2002) 1905
31. Hessian K.O., and Flynn B.L. Org. Lett. 5 (2003) 4377
32. Arcadi A., Cacchi S., Giuseppe S.D., Fabrizi G., and Marinelli F. Org. Lett. 4 (2002) 2409
33. Huang Q., Hunter J.A., and Larock R.C. J. Org. Chem. 67 (2002) 3437
34. Yao T., and Larock R.C. J. Org. Chem. 68 (2003) 5936
35. Yao T., Campo M.A., and Larock R.C. Org. Lett. 6 (2004) 2677
36. Yue D., Della C.N., and Larock R.C. Org. Lett. 6 (2004) 1581
37. Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 1432
38. Barluenga J., Trincado M., Marco-Arias M., Ballesteros A., Rubio E., and Gonzalez J.M. Chem. Commun. (2005) 2008
39. Fischer D., Tomeba H., Pahadi N.K., Patil N.T., and Yamamoto Y. Angew. Chem., Int. Ed. 46 (2007) 4764
40. Xie Y.-X., Liu X.-Y., Wu L.-Y., Han Y., Zhao L.-B., Fan M.-J., and Liang Y.-M. Eur. J. Org. Chem. (2008) 1013
41. Huang Q., Hunter J.A., and Larock R.C. Org. Lett. 3 (2001) 2973
42. For reviews, see:. Larock R.C. In: Diederich F., Stang P.J., and Tykwinski R.R. (Eds). Acetylene Chemistry (2005), Wiley-VCH, Weinheim 51-99
43. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079
44. Zeni G., and Larock R.C. Chem. Rev. 106 (2006) 4644
45. Huo Z., Tomeba H., and Yamamoto Y. Tetrahedron Lett. 49 (2008) 5531
46. Yeom H.-S., Kim S., and Shin S. Synlett (2008) 924
47. Ding Q., and Wu J. Adv. Synth. Catal. 350 (2008) 1850
48. 4) and filtered. Evaporation of the solvent followed by purification on silica gel provided the corresponding product 2.